WO2020117024A1 - Composition d'encapsulation - Google Patents

Composition d'encapsulation Download PDF

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Publication number
WO2020117024A1
WO2020117024A1 PCT/KR2019/017290 KR2019017290W WO2020117024A1 WO 2020117024 A1 WO2020117024 A1 WO 2020117024A1 KR 2019017290 W KR2019017290 W KR 2019017290W WO 2020117024 A1 WO2020117024 A1 WO 2020117024A1
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WO
WIPO (PCT)
Prior art keywords
layer
encapsulation
weight
film
sealing
Prior art date
Application number
PCT/KR2019/017290
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English (en)
Korean (ko)
Inventor
이승민
목영봉
문성남
양세우
Original Assignee
주식회사 엘지화학
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Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP19894083.5A priority Critical patent/EP3878903A4/fr
Priority to US17/299,222 priority patent/US20220029133A1/en
Priority to CN201980079999.4A priority patent/CN113166492B/zh
Priority to JP2021531789A priority patent/JP7354251B2/ja
Publication of WO2020117024A1 publication Critical patent/WO2020117024A1/fr

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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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    • B32B2250/24—All layers being polymeric
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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2255/00—Coating on the layer surface
    • B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2255/00—Coating on the layer surface
    • B32B2255/20—Inorganic coating
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
    • B32B2264/10—Inorganic particles
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    • B32B2264/10—Inorganic particles
    • B32B2264/104—Oxysalt, e.g. carbonate, sulfate, phosphate or nitrate particles
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    • B32B2307/00—Properties of the layers or laminate
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    • B32B2307/7244—Oxygen barrier
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    • B32B2307/7246—Water vapor barrier
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    • B32B2307/00—Properties of the layers or laminate
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    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/206—Organic displays, e.g. OLED
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08J2323/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08J2323/22—Copolymers of isobutene; butyl rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2206—Oxides; Hydroxides of metals of calcium, strontium or barium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers

Definitions

  • the present application relates to a sealing composition, a sealing film containing the same, an organic electronic device including the same, and a method of manufacturing the organic electronic device using the same.
  • An organic electronic device refers to a device including a layer of an organic material that generates an alternating charge using holes and electrons, and examples thereof include a photovoltaic device, a rectifier, and the like. And a transmitter and an organic light emitting diode (OLED).
  • an organic light emitting diode has less power consumption, a faster response speed, and is advantageous in thinning a display device or lighting compared to an existing light source.
  • OLED is excellent in space utilization, and is expected to be applied in various fields across various portable devices, monitors, laptops, and TVs.
  • the main problem is durability.
  • the organic material and metal electrode included in the OLED are very easily oxidized by external factors such as moisture. Therefore, products containing OLED are highly sensitive to environmental factors. Accordingly, various methods have been proposed to effectively block the penetration of oxygen or moisture from the outside to the organic electronic device such as OLED.
  • the present application provides an encapsulation composition, an encapsulation film comprising the same, and an organic electronic device including the same, which can effectively block moisture or oxygen flowing into the organic electronic device from the outside, and can implement an organic electronic device having an extremely small bezel portion. do.
  • the encapsulation composition may be applied to encapsulating or encapsulating organic electronic devices, such as OLEDs.
  • organic electronic device refers to an article or device having a structure including an organic material layer that generates an alternating charge by using holes and electrons between a pair of electrodes facing each other, for example
  • the photovoltaic device, a rectifier, a transmitter, an organic light emitting diode (OLED), and the like but are not limited thereto.
  • the organic electronic device may be an OLED.
  • An exemplary encapsulation composition may be a composition for encapsulating organic electronic devices.
  • the encapsulation composition may include a moisture absorbent surface-treated with an encapsulating resin and an aliphatic hydrocarbon compound.
  • the encapsulation resin may include an olefin-based resin. The present application can effectively block moisture even in harsh conditions by including the resin and a specific moisture adsorbent.
  • the encapsulating resin may be a crosslinkable resin or a curable resin.
  • the resin may be a photocurable resin or a thermosetting resin.
  • the encapsulating resin may have a glass transition temperature of less than 0°C, less than -10°C or less than -30°C, less than -50°C, or less than -60°C. The lower limit is not particularly limited, but may be -100°C or higher.
  • the glass transition temperature may be a glass transition temperature after curing or crosslinking for the encapsulating resin alone composition.
  • the present application may include an olefin-based resin as the sealing resin.
  • the olefin-based resin may include a homopolymer or a copolymer of the olefin-based compound.
  • the encapsulating resin may be a polymer derived from butylene.
  • the term "polymer derived from butylene" may mean that one or more polymerized units of the polymer are made from butylene. Since the polymer derived from butylene is very low in polarity, is transparent, and has little effect of corrosion, when used as an encapsulant or a sealing material, it is possible to realize excellent moisture blocking properties and durability reliability.
  • the polymer derived from butylene is also a homopolymer of butylene monomer; A copolymer obtained by copolymerizing a butylene monomer with another polymerizable monomer; Reactive oligomers using butylene monomers; Or mixtures thereof.
  • the polymer derived from the present application may mean that the monomer forms a polymer in polymerized units.
  • the butylene monomer may include, for example, 1-butene, 2-butene or isobutylene.
  • Other monomers polymerizable with the butylene monomer or derivative may include, for example, isoprene, styrene or butadiene.
  • the copolymer By using the copolymer, physical properties such as fairness and crosslinking degree can be maintained, and thus heat resistance of the sealing composition itself can be secured when applied to an organic electronic device.
  • the reactive oligomer using a butylene monomer may include a butylene polymer having a reactive functional group.
  • the oligomer may have a weight average molecular weight of 500 to 5000 g/mol.
  • the butylene polymer may be combined with other polymers having reactive functional groups.
  • the other polymer may be an alkyl (meth)acrylate, but is not limited thereto.
  • the reactive functional group may be a hydroxy group, a carboxyl group, an isocyanate group or a nitrogen-containing group.
  • the reactive oligomer and the other polymer may be crosslinked by a polyfunctional crosslinking agent, and the multifunctional crosslinking agent may be at least one selected from the group consisting of isocyanate crosslinking agents, epoxy crosslinking agents, aziridine crosslinking agents, and metal chelate crosslinking agents.
  • the polymer derived from butylene of the present application may be a copolymer of a diene compound and an olefin-based compound comprising one carbon-carbon double bond.
  • a copolymer may include an unsaturated group such as a double bond in the encapsulating resin main chain.
  • the olefin-based compound may include butylene
  • the diene may be a polymerizable monomer with the olefin-based compound, and may include, for example, isoprene or butadiene.
  • the copolymer of diene and olefinic compound containing one carbon-carbon double bond may be butyl rubber.
  • the polymer may have a weight average molecular weight (MW.) of the degree that the pressure-sensitive adhesive composition can be molded into a film shape.
  • MW. weight average molecular weight
  • the polymer is about 10,000 to 2 million g/mol, 100,000 to 1.5 million g/mol, 150,000 to 1.3 million g/mol, 330,000 to 1 million g/mol, or 350,000 to 900,000 g It may have a weight average molecular weight of about /mol.
  • the term weight average molecular weight means a conversion value for standard polystyrene measured by GPC (Gel permeation Chromatograph).
  • the resin component does not necessarily have the above-mentioned weight average molecular weight.
  • a separate binder resin may be blended into the composition.
  • the terms polymer and resin component may be used in the same sense.
  • the encapsulation composition of the present application may include a moisture absorbent.
  • moisture absorbent in the present specification may mean, for example, a chemically reactive adsorbent capable of removing the above through chemical reaction with moisture or moisture that has penetrated into the encapsulation film.
  • the moisture adsorbent may be surface treated with an aliphatic hydrocarbon compound, and the aliphatic hydrocarbon compound may include at least one polar functional group.
  • the polar functional group may include, for example, hydroxy group, carboxyl group, amine group, acrylic group, methacryl group, aldehyde group, epoxy group, anhydride group, amide group, phosphoric acid group (Phosphate) or a combination thereof.
  • the present application increases the compatibility with the above-mentioned encapsulating resin, by using the moisture adsorbent, thereby achieving excellent moisture barrier performance.
  • the moisture adsorbent may be surrounded by an aliphatic hydrocarbon compound on the surface.
  • the aliphatic hydrocarbon compound may be, for example, a compound containing a polar functional group in a molecular structure, and the structure is not particularly limited as long as it has the polar functional group.
  • the polar functional group may be located at the end of the aliphatic hydrocarbon compound.
  • the aliphatic hydrocarbon compound may be a compound having a range of 5 to 50 carbon atoms or 10 to 40 carbon atoms, and the compound may have a straight chain, branched chain, or cyclic structure.
  • the lower limit of the carbon number may be, for example, 8, 10, 13, 15, 16 or 17 or more, and the upper limit may be, for example, 45, 40, 35, 30, 28, 25, 23, 20, 19 or 18 or less.
  • the structure in which the aliphatic hydrocarbon compound surrounds the surface of the water adsorbent may have a structure in which the polar functional group is present on the surface in contact with the water adsorbent, and the non-polar main chain extends through the polar functional group.
  • the above structure increases the compatibility between the water adsorbent and the encapsulating resin, can realize excellent water blocking performance, and can disperse a large amount of water adsorbent compared to the prior art.
  • the aliphatic hydrocarbon compound may be one of surfactants, and is not particularly limited as long as it has the above structure.
  • surfactants for example, stearic acid, palmitic acid, oleic acid, oleic acid Oleylamine, octadecylamine, araeze acid, linoleic acid, dibutyl phosphate, lauryl-4-carboxylic acid acid), lauryl-6-carboxylic acid or lauryl-11-carboxylic acid.
  • the water adsorbent may be pulverized in the form of particles to be evenly dispersed in the bag composition.
  • the evenly dispersed state may mean a state in which a water adsorbent is present at the same or substantially the same density in any part of the sealing composition.
  • the water adsorbent that can be used in the above include metal oxides, sulfates, or organic metal oxides.
  • the sulfate include magnesium sulfate, sodium sulfate, or nickel sulfate
  • examples of the organic metal oxide include aluminum oxide octylate and the like.
  • metal oxide in the above phosphorus pentoxide (P 2 O 5 ), lithium oxide (Li 2 O), sodium oxide (Na 2 O), barium oxide (BaO), calcium oxide (CaO) or magnesium oxide (MgO ), and examples of the metal salt include lithium sulfate (Li 2 SO 4 ), sodium sulfate (Na 2 SO 4 ), calcium sulfate (CaSO 4 ), magnesium sulfate (MgSO 4 ), and cobalt sulfate (CoSO 4 ), Sulfates such as gallium sulfate (Ga 2 (SO 4 ) 3 ), titanium sulfate (Ti(SO 4 ) 2 ) or nickel sulfate (NiSO 4 ), calcium chloride (CaCl 2 ), magnesium chloride (MgCl 2 ), strontium chloride (SrCl) 2 ), yttrium chloride (YCl 3 ), copper chloride (CuCl 2 ),
  • moisture adsorbent that may be included in the encapsulation composition
  • one type of the above-described configuration may be used, or two or more types may be used.
  • calcined dolomite or the like may be used.
  • Such a water adsorbent can be controlled to an appropriate size according to the application.
  • the average particle diameter of the water adsorbent may be controlled to 8 ⁇ m or less, 7 ⁇ m or less, and 6 ⁇ m or less.
  • the lower limit is not particularly limited, but may be 0.1 ⁇ m, 0.5 ⁇ m, or 1 ⁇ m.
  • the particle diameter may be measured by particle size analysis according to D90.
  • the moisture adsorbent having the size in the above range is not too fast to react with moisture, so it is easy to store, and can effectively remove moisture without damaging the device to be sealed.
  • the water adsorbent having a smaller particle size than the conventional one may be dispersed in the encapsulation composition in a larger amount than the conventional one.
  • the content of the water adsorbent is not particularly limited and may be appropriately selected in consideration of the desired barrier properties.
  • the water adsorbent is 150 to 15000 parts by weight, 180 to 1400 parts by weight, 220 to 1300 parts by weight, 250 to 1200 parts by weight, 280 to 1100 parts by weight, or 300 to 1000 parts by weight based on 100 parts by weight of the encapsulating resin It may be included in parts by weight.
  • the present application may include a large amount of water adsorbent as compared to the prior art, thereby achieving excellent moisture barrier performance. Conventionally, when a large amount of water adsorbent is included as described above, aggregation or deposition occurs or interlayer cracking occurs when formed into a film, but the present application can solve this problem by using the specific water adsorbent.
  • the sealing composition may further include a tackifier, and the tackifier may have a softening point of 145°C or less or 130°C or less.
  • the softening point of the tackifier may be, for example, in the range of 20°C to 130°C or 50°C to 125°C.
  • the weight average molecular weight of the tackifier may be in the range of about 300 to 5,000 g/mol or 500 to 3500 g/mol.
  • the tackifier may be a polymer polymerized from a monomer having a carbon number in the range of 3 to 15 or 5 to 10 within the molecular structure.
  • the tackifier may have a ring structure within the molecular structure, and the ring structure may be a single ring structure, but is not limited thereto, and may have a bicyclic or tricyclic structure.
  • the present application can realize excellent physical compatibility with the encapsulation resin described above, thereby realizing the desired properties in the present application.
  • the softening point in the present specification may be measured according to ASTM E28 standard, unless otherwise specified.
  • the tackifier may include, for example, piperylene compound, styrene compound, alpha methyl styrene compound, isoprene compound, cyclopentadiene compound or dicyclopentadiene compound.
  • the content of the tackifier can be appropriately adjusted as needed.
  • the tackifier may be included in the range of 140 to 450 parts by weight, 149 to 410 parts by weight, or 150 to 405 parts by weight based on 100 parts by weight of the encapsulating resin.
  • the tackifier of the present application is excellent in compatibility with the above-mentioned specific encapsulation resin and water adsorbent, and accordingly, the content range of the tackifier can be adjusted higher than in the prior art, thereby improving the adhesion performance of the film with moisture barrier properties. Implement efficiently.
  • the encapsulation composition of the present application may include an active energy ray polymerizable compound capable of being polymerized by irradiation with active energy rays together with the encapsulation resin described above.
  • the active energy ray polymerizable compound is, for example, a functional group capable of participating in a polymerization reaction by irradiation of active energy rays, for example, a functional group comprising an ethylenically unsaturated double bond such as an acryloyl group or a methacryloyl group.
  • It may mean a compound containing one or more or two or more functional groups such as an epoxy group or an oxetane group.
  • the present application allows the encapsulating resin to have an unsaturated group before curing or crosslinking, and the unsaturated group can participate in crosslinking together when crosslinking the polyfunctional active energy ray polymerizable compound.
  • the sealing composition of the present application is highly compatible with the sealing resin, and includes an active energy ray polymerizable compound capable of forming a specific crosslinking structure with the sealing resin, and thus may be cured or crosslinked.
  • the active energy ray polymerizable compound may be a polyfunctional active energy ray polymerizable compound, for example, a multifunctional acrylate (MFA).
  • MFA multifunctional acrylate
  • the polyfunctional active energy ray polymerizable compound capable of being polymerized by irradiation with the active energy ray may satisfy Formula 1 below.
  • the active energy ray polymerizable compound is 2 parts by weight to 35 parts by weight, 3 to 30 parts by weight, 5 parts by weight to 25 parts by weight, 8 parts by weight to 20 parts by weight, 10 parts by weight based on 100 parts by weight of the encapsulating resin It may be included in 18 to 18 parts by weight or 12 to 18 parts by weight.
  • R 1 is hydrogen or an alkyl group having 1 to 4 carbon atoms
  • n is a number of 2 to 10 or 2 to 6
  • X is a residue derived from a straight chain, branched chain or cyclic alkyl group having 3 to 30 carbon atoms. Indicates.
  • X when X is a residue derived from a cyclic alkyl group, X may be, for example, a residue derived from a cyclic alkyl group having 3 to 30 carbon atoms, 6 to 28 carbon atoms, 8 to 22 carbon atoms, or 12 to 20 carbon atoms. have.
  • X when X is a residue derived from a straight-chain alkyl group, X may be a residue derived from a straight-chain alkyl group having 3 to 30 carbon atoms, 6 to 25 carbon atoms, or 8 to 20 carbon atoms. Further, when X is a residue derived from a branched chain alkyl group, X may be a residue derived from a branched chain alkyl group having 3 to 30 carbon atoms, 5 to 25 carbon atoms, or 6 to 20 carbon atoms.
  • residue derived from an alkyl group means a residue of a specific compound, and may mean an alkyl group.
  • X when n is 2, X may be an alkylene group.
  • X when n is 3 or more, X may be attached to the (meth) acroyl group of Formula 1 by removing two or more hydrogens of the alkyl group.
  • alkyl group in the present specification, unless otherwise specified, has 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. It may mean an alkyl group.
  • the alkyl group may have a straight chain, branched chain, or cyclic structure, and may be optionally substituted by one or more substituents.
  • alkylene group in this specification, unless specifically specified otherwise, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 10 carbon atoms, or carbon atoms It may mean an alkylene group of 2 to 8.
  • the alkylene group may have a straight chain, branched chain, or cyclic structure, and may be optionally substituted by one or more substituents.
  • the active energy ray polymerizable compound capable of being polymerized by irradiation with the active energy ray may be used without limitation as long as the formula (1) is satisfied.
  • the compound is 1,4-butanediol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8- Octanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, cyclo Hexane-1,4-dimethanol di(meth)acrylate, tricyclodecanedimethanol (meth)diacrylate, dimethylol dicyclopentane di(meth)acrylate, neopentyl glycol modified trimethylpropane di(meth)acrylic Rate, adam
  • the weight average molecular weight may be less than 1,000 g/mol, 800 g/mol or less, or 450 g/mol or less, and the lower limit is, for example, 100 g/mol or more.
  • a compound containing two or more functional groups can be used.
  • the ring structure included in the active energy ray polymerizable compound includes a carbocyclic structure or a heterocyclic structure; Or it may be a monocyclic or polycyclic structure.
  • the encapsulation composition may further include a radical initiator that can induce the polymerization reaction of the above-mentioned active energy ray polymerizable compound.
  • the radical initiator can be a photoinitiator or a thermal initiator.
  • the specific type of photoinitiator may be appropriately selected in consideration of the curing rate and the possibility of yellowing.
  • benzoin-based, hydroxy-ketone-based, amino-ketone-based or phosphine oxide-based photoinitiators can be used, and specifically, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether , Benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethylano acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2 -Hydroxy-2-methyl-1-phenylpropan-1one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propane-1- On, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, benzophenone, p-phenylbenzophenone, 4,4'
  • the radical initiator may be included in a proportion of 0.2 parts by weight to 20 parts by weight based on 100 parts by weight of the active energy ray polymerizable compound.
  • the encapsulation composition may also include an inorganic filler, if desired.
  • an inorganic filler may refer to a material that has no reactivity with moisture or is lower than the above-described moisture adsorbent, but can block or hinder the movement of moisture or moisture in the film.
  • the inorganic filler for example, one or two or more of clay, talc, silica, acicular silica, plate silica, porous silica, zeolite, titania or zirconia can be used.
  • the inorganic filler may be surface treated with an organic modifier or the like to facilitate penetration of organic substances.
  • Such organic modifiers include, for example, dimethyl benzyl hydrogenated tallow quaternaty ammonium, dimethyl dihydrogenated tallow quaternary ammonium, methyl tallow bis-2-hydroxyethyl Methyl tallow bis-2-hydroxyethyl quaternary ammonium, dimethyl hydrogenated tallow 2-ethylhexyl quaternary ammonium, dimethyl dehydrogenated tallow quaternary ammonium ) Or a mixture thereof, an organic modifier, and the like.
  • the content of the inorganic filler is not particularly limited, and may be appropriately selected in consideration of desired barrier properties.
  • the inorganic filler may be included in 5 to 100 parts by weight based on 100 parts by weight of the sealing resin.
  • the sealing composition may include various additives according to uses and manufacturing processes described below.
  • the encapsulation composition may be solid or semi-solid at room temperature in a cured or uncured state.
  • room temperature in the present specification may be a temperature of about 15°C to 35°C, 20°C to 30°C, or about 25°C.
  • the present application also relates to a sealing film.
  • the encapsulation film may include an encapsulation layer including the encapsulation composition described above.
  • the encapsulation layer may be a single layer or a multilayer structure of two or more layers.
  • the encapsulation resin may be included in an amount of 5 wt% or more, 10 to 85 wt%, 12 to 83 wt%, 15 to 80 wt%, 17 to 78 wt%, or 20 to 73 wt% of the total resin component weight in the encapsulation layer.
  • the resin component may include the encapsulating resin or the aforementioned tackifier (tackifier resin).
  • the sealing layer may be a pressure-sensitive adhesive or an adhesive containing the above components, and the aforementioned sealing composition may be a pressure-sensitive adhesive composition or an adhesive composition.
  • the encapsulation layer may be a single layer or a multilayer structure of two or more layers.
  • the encapsulation resin may be included in at least one of the two or more encapsulation layers.
  • the content of the moisture adsorbent can be controlled to prevent physical and chemical damage to the device.
  • a small amount of a water adsorbent may be included in the encapsulation layer facing the device, or it may not contain a water absorbent.
  • the second layer may include 0 to 20% moisture adsorbent relative to the total mass of the moisture adsorbent contained in the encapsulation film.
  • the encapsulation film is an organic electronic device
  • the encapsulation layer formed on one surface of the second layer is defined as a first layer
  • the first layer is an encapsulation film. It may contain 80 to 100% of the water adsorbent relative to the total mass of the water adsorbent containing.
  • the present application may have a ratio of the thickness of the first layer to the thickness of the second layer in the range of 1.2 to 8 or 1.5 to 5. In this structure, the present application can realize the stability of the organic electronic device while maximizing the moisture barrier performance.
  • the stacking order of the second layer and the first layer additionally stacked is not particularly limited.
  • the encapsulation film may be composed of three or more layers, for example, the first layer may be included as two or more layers, or the second layer may be included as two or more layers.
  • the encapsulation film may further include a metal layer.
  • the metal layer may be a single layer or two or more multilayer structures. At least one of the metal layers may have, for example, a thermal conductivity of 50 to 800 W/mK. In addition, at least one of the metal layers may have a coefficient of linear expansion of 20 ppm/°C or less.
  • the metal layer has a thermal conductivity of 50 W/mK or more, 80 W/mK or more, 90 W/mK or more, 100 W/mK or more, 110 W/mK or more, 120 W/mK or more, 130 W/mK or more, 140 W/mK or more, 150 W/mK or more, 200 W/mK or more, or 210 W/mK or more.
  • the upper limit of the thermal conductivity is not particularly limited, and may be 800 W/mK or less or 700 W/mK or less. As described above, since at least one metal layer has high thermal conductivity, heat generated at the bonding interface during the metal layer bonding process can be released more quickly.
  • the thermal conductivity may be measured at any one of the temperature range of 0 to 30 °C.
  • thermal conductivity is a degree that indicates the ability of a material to transfer heat by conduction, and the unit can be expressed in W/mK.
  • the unit represents the degree of heat transfer of a substance at the same temperature and distance, and means a unit of heat (watt) for a unit of distance (meter) and a unit of temperature (Calvin).
  • the thermal conductivity may refer to thermal conductivity when measured according to ASTM E1461.
  • the thermal conductivity can be calculated using a thermal diffusivity measured according to ASTM E1461 and a known specific heat value.
  • At least one of the metal layers has a linear expansion coefficient of 20 ppm/°C or less, 18 ppm/°C or less, 15 ppm/°C or less, 13 ppm/°C or less, 9 ppm/°C or less, 5 ppm/°C or less Or 3 ppm/°C or less.
  • the lower limit of the preceding window coefficient is not particularly limited, but may be 0 ppm/°C or higher or 0.1 ppm/°C or higher.
  • the present application can realize dimensional stability and durability reliability of the film in a panel driven at high temperature by adjusting the linear expansion coefficient of the metal layer.
  • the coefficient of linear expansion can be measured according to the standard according to ASTM E831.
  • the metal layer thickness of the encapsulation film may be in the range of 3 ⁇ m to 500 ⁇ m, 10 ⁇ m to 450 ⁇ m, 20 ⁇ m to 400 ⁇ m, 30 ⁇ m to 350 ⁇ m, or 40 ⁇ m to 200 ⁇ m.
  • the metal layer may have metal deposited on a thin metal foil or a polymer substrate layer.
  • the metal layer is not particularly limited as long as it satisfies the aforementioned thermal conductivity or coefficient of linear expansion and is a material containing a metal.
  • the metal layer may include any one of metal, metal oxide, metal nitride, metal carbide, metal oxynitride, metal oxyboride, and combinations thereof.
  • the metal layer may include an alloy in which one or more metal elements or nonmetal elements are added to one metal, and may include, for example, Invar and stainless steel (SUS).
  • the metal layer is iron, chromium, copper, aluminum nickel, iron oxide, chromium oxide, silicon oxide, aluminum oxide, titanium oxide, indium oxide, tin oxide, indium tin oxide, tantalum oxide, zirconium oxide, niobium oxide , And combinations thereof.
  • the metal layer can be deposited by electrolytic, rolling, heat evaporation, electron beam evaporation, sputtering, reactive sputtering, chemical vapor deposition, plasma chemical vapor deposition or electron cyclotron resonance source plasma chemical vapor deposition means.
  • the metal layer may be deposited by reactive sputtering.
  • the sealing film of the present application may further include a protective layer formed on the metal layer.
  • the protective layer may include a resin component.
  • the material constituting the protective layer is not particularly limited.
  • the protective layer may be a moisture-proof layer that can block moisture permeation.
  • an adhesive or an adhesive may be further included between the protective layer and the metal layer.
  • the material of the pressure-sensitive adhesive or adhesive is not particularly limited, and a known material can be used.
  • the pressure-sensitive adhesive or adhesive may be an acrylic-based, epoxy-based, urethane-based, silicone-based, or rubber-based adhesive or adhesive.
  • the material of the pressure-sensitive adhesive or adhesive may be the same as or different from the material of the above-described sealing layer.
  • the encapsulation film further includes a base film or a release film (hereinafter, sometimes referred to as a "first film”), wherein the encapsulation layer is formed on the substrate or release film. It can have a structure.
  • the structure may further include a base material or a release film (hereinafter, sometimes referred to as a "second film”) formed on the encapsulation layer or the metal layer.
  • 1 is a cross-sectional view showing an exemplary encapsulation film 10 including an encapsulation layer 11 formed on a base film or release film 1.
  • FIG. 2 is a cross-sectional view showing an exemplary encapsulation film 10 including the above-described metal layer 12 formed on the encapsulation layer 11 and the above-described protective layer 13 formed on the metal layer.
  • the specific type of the first film that can be used in the present application is not particularly limited.
  • the first film for example, a general polymer film in this field can be used.
  • the substrate or release film polyethylene terephthalate film, polytetrafluoroethylene film, polyethylene film, polypropylene film, polybutene film, polybutadiene film, vinyl chloride copolymer film, polyurethane film , Ethylene-vinyl acetate film, ethylene-propylene copolymer film, ethylene-ethyl acrylate copolymer film, ethylene-methyl acrylate copolymer film or polyimide film, and the like can be used.
  • an appropriate release treatment may be performed on one or both surfaces of the base film or release film of the present application.
  • the release agent used for the release treatment of the base film an alkyd-based, silicone-based, fluorine-based, unsaturated ester-based, polyolefin-based or wax-based, etc. may be used.
  • an alkyd-based, silicone-based or fluorine-based mold release agent is used. It is preferred, but is not limited thereto.
  • the thickness of the base film or release film (first film) as described above is not particularly limited, and may be appropriately selected according to the applied application.
  • the thickness of the first film in the present application may be about 10 ⁇ m to 500 ⁇ m, preferably about 20 ⁇ m to 200 ⁇ m. If the thickness is less than 10 ⁇ m, there is a possibility that deformation of the base film easily occurs in the manufacturing process, and when it exceeds 500 ⁇ m, economic efficiency is deteriorated.
  • the thickness of the encapsulation layer included in the encapsulation film of the present application is not particularly limited, and may be appropriately selected according to the following conditions in consideration of the application to which the film is applied.
  • the thickness of the encapsulation layer may be about 5 ⁇ m to 200 ⁇ m, 10 ⁇ m to 100 ⁇ m, and 15 ⁇ m to 60 ⁇ m.
  • the thickness may mean the thickness of the multilayer when the encapsulation layer is multilayer.
  • the thickness of the encapsulation layer is less than 5 ⁇ m, sufficient moisture blocking ability cannot be exhibited, and when it exceeds 200 ⁇ m, it is difficult to secure fairness, and due to moisture reactivity, the thickness expansion is large, which can damage the deposited film of the organic light emitting device and can be economical. Falls.
  • the present application also relates to an organic electronic device.
  • the organic electronic device as shown in Figure 3, the substrate 21; An organic electronic element 22 formed on the substrate 21; And it may include the above-described sealing film 10 for sealing the front of the organic electronic device (22).
  • the encapsulation film may encapsulate the front surface, for example, both the top and side surfaces of the organic electronic device formed on the substrate.
  • the encapsulation film 10 may include an encapsulation layer 11 containing the encapsulation composition in a crosslinked or cured state.
  • an organic electronic device may be formed such that the encapsulation layer contacts the front surface of the organic electronic device.
  • the organic electronic device may be, for example, an organic light emitting device.
  • the encapsulation layer may be formed as a structural adhesive that effectively fixes and supports the substrate and the metal layer while exhibiting excellent moisture barrier properties in an organic electronic device.
  • 3 is an encapsulation layer 11.
  • the encapsulation film 10 including the metal layer 12 and the protective layer 13 integrally is a cross-sectional view of an exemplary organic electronic device in which the organic electronic device 22 is completely encapsulated.
  • the encapsulation layer may be formed of a stable encapsulation layer irrespective of the form of an organic electronic device such as top emission or bottom emission.
  • the organic electronic device of the present application may include a passivation layer.
  • the protective film is to prevent damage to the electrode of the device, may be made of a conventional material in the art, for example, may include SiNx or Al 2 O 3 as an inorganic material.
  • the passivation layer may be a passivation layer in which organic and inorganic layers are alternately deposited.
  • the present application also provides a method of manufacturing an organic electronic device.
  • the manufacturing method may include applying the encapsulation film described above to the substrate on which the organic electronic device is formed to cover the organic electronic device.
  • the manufacturing method may further include a step of curing or crosslinking the encapsulation film.
  • the curing or crosslinking step of the encapsulation film means curing or crosslinking of the encapsulation layer, and the curing may be performed before or after the encapsulation film covers the organic electronic device.
  • the term "curing” may mean that the sealing layer of the present invention is formed in the form of an adhesive by heating or UV irradiation process or the like to form a crosslinked structure. Alternatively, it may mean that the adhesive composition is solidified and adhered as an adhesive.
  • the manufacturing method is to form a transparent electrode by a method such as vacuum deposition or sputtering on a glass or polymer film used as a substrate, for example, a hole transport layer, a light emitting layer and an electron transport layer on the transparent electrode
  • a transparent electrode by a method such as vacuum deposition or sputtering on a glass or polymer film used as a substrate, for example, a hole transport layer, a light emitting layer and an electron transport layer on the transparent electrode
  • an electrode layer may be additionally formed thereon to form an organic electronic device.
  • the front surface of the organic electronic device of the substrate subjected to the above process may be positioned to cover the encapsulation layer of the encapsulation film.
  • the present application provides an encapsulation composition, an encapsulation film comprising the same, and an organic electronic device including the same, which can effectively block moisture or oxygen flowing into the organic electronic device from the outside, and can implement an organic electronic device having an extremely small bezel portion. do.
  • FIG. 1 and 2 are cross-sectional views showing an encapsulation film according to one example of the present application.
  • FIG. 3 is a cross-sectional view showing an organic electronic device according to an example of the present application.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • the solution of the first layer prepared above was applied to the release surface of release PET and dried at 110° C. for 10 minutes to form a layer having a thickness of 40 ⁇ m.
  • the solution of the second layer prepared above was applied to the release surface of the release PET, and dried at 130° C. for 3 minutes to form a layer having a thickness of 10 ⁇ m.
  • the two layers were plywood to prepare an encapsulation film having a two-layer encapsulation layer.
  • the release-treated PET was peeled on the surface of the first layer of the two-layer encapsulation layer prepared above, and the encapsulation layer was plywood so that the prepared metal layer (aluminum) was in contact with the first layer.
  • a cut film of a desired shape was manufactured by knife cutting the plywood-metal integral sealing film.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • CaO (Aldrich) surface-treated with stearic acid was mixed with toluene as a solvent to prepare a water adsorbent solution at a concentration of 50% by weight of solids.
  • a sealing film was prepared in the same manner as in Example 1, except that the first layer solution was prepared as follows.
  • a sealing film was prepared in the same manner as in Example 1, except that the surface was treated with an epoxy-based silane coupling agent ((3-Glycidyloxypropyl)trimethoxysilane) instead of stearic acid on the surface as a water adsorbent.
  • an epoxy-based silane coupling agent ((3-Glycidyloxypropyl)trimethoxysilane) instead of stearic acid on the surface as a water adsorbent.
  • the coating appearance of the encapsulation film prepared in Examples and Comparative Examples was visually observed to classify as X when agglomeration of moisture adsorbent particles occurred, and classified as O when excellent appearance without agglomeration.
  • the encapsulation film prepared in Examples and Comparative Examples was laminated on a glass substrate on which an organic electronic device was formed, and the encapsulation layer was covered so as to cover the device. It was prepared. Thereafter, the sealing film was peeled off again, and the appearance was observed. It was classified as O when there were no bubbles generated, O when there were 3 or fewer bubbles, and X when more than 3 bubbles occurred.
  • Example 2 Calcium was deposited on a glass substrate having a size of 100 mm x 100 mm to a size of 5 mm x 5 mm and a thickness of 100 nm, and sealing films of Examples and Comparative Examples were attached to cover the entire surface of the calcium.
  • the obtained specimens were observed in a constant-temperature and constant-humidity chamber at 85°C and 85% relative humidity to observe the point at which calcium began to become transparent by the oxidation reaction due to moisture penetration.
  • O is indicated when the initiation time is 700 hours or more, ⁇ when the initiation time is 700 hours or less, and when the initiation time is 500 hours or more, and X when the initiation time is less than 500 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Analytical Chemistry (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Electroluminescent Light Sources (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Sealing Material Composition (AREA)
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Abstract

La présente invention porte sur une composition d'encapsulation, un film d'encapsulation comprenant cette composition, un dispositif électronique organique la comprenant et un procédé de fabrication d'un dispositif électronique organique l'utilisant. La composition d'encapsulation peut bloquer efficacement l'humidité ou l'oxygène introduit dans un dispositif électronique organique depuis l'extérieur, et permet la mise en oeuvre d'un dispositif électronique organique ayant une très petite partie de cadran. [Dessin représentatif] Figure 1
PCT/KR2019/017290 2018-12-07 2019-12-09 Composition d'encapsulation WO2020117024A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP19894083.5A EP3878903A4 (fr) 2019-12-09 Composition d'encapsulation
US17/299,222 US20220029133A1 (en) 2018-12-07 2019-12-09 Encapsulation composition
CN201980079999.4A CN113166492B (zh) 2018-12-07 2019-12-09 封装组合物
JP2021531789A JP7354251B2 (ja) 2018-12-07 2019-12-09 封止組成物

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KR10-2018-0157182 2018-12-07
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JP (1) JP7354251B2 (fr)
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CN (1) CN113166492B (fr)
TW (1) TWI813827B (fr)
WO (1) WO2020117024A1 (fr)

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TWI813827B (zh) 2023-09-01
JP2022511037A (ja) 2022-01-28
TW202035548A (zh) 2020-10-01
KR20230152613A (ko) 2023-11-03
CN113166492B (zh) 2023-07-28
CN113166492A (zh) 2021-07-23
JP7354251B2 (ja) 2023-10-02
US20220029133A1 (en) 2022-01-27
KR20200070140A (ko) 2020-06-17
KR102626267B1 (ko) 2024-01-18
EP3878903A1 (fr) 2021-09-15

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